Interconversion of dipoles by the flash vacuum pyrolysis of oxadiazolinones

Padwa, Albert; Caruso, Thomas P.; Nahm, Steven; Rodrı́guez, Augusto

doi:10.1021/ja00374a028

Cited by 43 publications

(10 citation statements)

References 6 publications

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“…These results agree with previous ones. 23 Compound 6 was identified by comparison with an authentic sample. 1 H NMR (DMSO-d6), δ (ppm) 7.65 (4H, m), 8.05 (4H, m).…”

Section: Methodsmentioning

confidence: 99%

Flash Vacuum Pyrolysis of Pyrazoles as an Alternative Way to Study Vinylcarbenes

1998

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Flash vacuum pyrolysis (FVP) reactions of 3,5-diphenylpyrazole (1) and 3(5)-methyl-5(3)-phenylpyrazole (2) were carried out. The reaction products expected for nitrogen extrusion were formed through different rearrangements in the vinylcarbene intermediate. Kinetic parameters for nitrogen extrusion from 1 are reported. To show that FVP reactions of pyrazoles are useful to obtain vinylcarbenes, the reactions of other pyrazoles previously studied are also discussed.

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“…These results agree with previous ones. 23 Compound 6 was identified by comparison with an authentic sample. 1 H NMR (DMSO-d6), δ (ppm) 7.65 (4H, m), 8.05 (4H, m).…”

Section: Methodsmentioning

confidence: 99%

Flash Vacuum Pyrolysis of Pyrazoles as an Alternative Way to Study Vinylcarbenes

1998

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“…The starting materials, 5‐aryl‐1,3,4‐oxadiazol‐2(3 H )‐ones ( 5a – 5d ) , were prepared in good yields by cyclization of compounds 4a – 4d under reflux conditions using POCl 3 . Our study started with the reaction between 5‐aryl‐1,3,4‐oxadiazol‐2(3 H )‐ones ( 5a – 5d ) and propargyl bromide in the presence of NaH in tetrahydrofuran/dimethylformamide (1:1) to obtain the 5‐aryl‐3‐(prop‐2‐ynyl)‐1,3,4‐oxadiazol‐2(3 H )‐ones ( 6a – 6d ) . In the second step, these N ‐propargylated compounds 6a – 6d were independently reacted with various azides using “click” chemistry and aldoximes, respectively giving novel 3‐((1‐benzyl‐1 H ‐1,2,3‐triazol‐4‐yl)methyl)‐5‐aryl‐1,3,4‐oxadiazol‐2(3 H )‐one hybrids ( 7a – 7h ) and 5‐aryl‐3‐((3‐arylisoxazol‐5‐yl)methyl)‐1,3,4‐oxadiazol‐2(3 H )‐one hybrids ( 8a – 8i ) in good yields (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and In Vitro Anticancer Activity of Novel 1,3,4‐Oxadiazole‐Linked 1,2,3‐Triazole/Isoxazole Hybrids

Madhavilatha

Bhattacharjee

Sabitha

et al. 2018

Journal of Heterocyclic Chem

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“…Compound 6 was prepared as shown in Scheme I. We had speculated that 10 could undergo rearrangement to give vinylferrocene (11) in analogous fashion to that of o-tolylcarbene (12) to give styrene (13) 6Ktindig, E. P.; Bernardinelli, G.; Leresche, J.; Romanens, P. Angew. Chem., 1990, 102, 421-3; Angew.…”

Section: Discussionmentioning

confidence: 99%

Thermally-generated reactive intermediates: Trapping of the parent ferrocene-based o-quinodimethane and reactions of diradicals generated by hydrogen-atom transfers

Ferguson

1993

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, "Thermally-generated reactive intermediates: trapping of the parent ferrocene-based o-quinodimethane and reactions of diradicals generated by hydrogen-atom transfers " (1993). Retrospective Theses and Dissertations. 10303. http://lib.dr.iastate.edu/rtd/10303 INFORMATION TO USERSThis manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer.The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction.In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion.Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book.Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6" x 9" black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. University Microfilms International 1993Signature was redacted for privacy.Signature was redacted for privacy.Signature was redacted for privacy.

show abstract

Interconversion of dipoles by the flash vacuum pyrolysis of oxadiazolinones

Cited by 43 publications

References 6 publications

Flash Vacuum Pyrolysis of Pyrazoles as an Alternative Way to Study Vinylcarbenes

Flash Vacuum Pyrolysis of Pyrazoles as an Alternative Way to Study Vinylcarbenes

Synthesis and In Vitro Anticancer Activity of Novel 1,3,4‐Oxadiazole‐Linked 1,2,3‐Triazole/Isoxazole Hybrids

Thermally-generated reactive intermediates: Trapping of the parent ferrocene-based o-quinodimethane and reactions of diradicals generated by hydrogen-atom transfers

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